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Acetaminophen

Base Information Edit
  • Chemical Name:Acetaminophen
  • CAS No.:103-90-2
  • Deprecated CAS:8055-08-1,719293-04-6,1430221-00-3,719293-04-6
  • Molecular Formula:C8H9NO2
  • Molecular Weight:151.165
  • Hs Code.:2924.29
  • European Community (EC) Number:203-157-5
  • ICSC Number:1330
  • NSC Number:755853,109028,3991
  • UNII:362O9ITL9D
  • DSSTox Substance ID:DTXSID2020006
  • Nikkaji Number:J4.025H
  • Wikipedia:Paracetamol,Acetaminophen
  • Wikidata:Q57055,Q83003217
  • NCI Thesaurus Code:C198
  • RXCUI:161
  • Pharos Ligand ID:W4WH4FK6P232
  • Metabolomics Workbench ID:37895
  • ChEMBL ID:CHEMBL112
  • Mol file:103-90-2.mol
Acetaminophen

Synonyms:Acamol;Acephen;Acetaco;Acetamidophenol;Acetaminophen;Acetominophen;Algotropyl;Anacin 3;Anacin-3;Anacin3;APAP;Datril;Hydroxyacetanilide;N-(4-Hydroxyphenyl)acetanilide;N-Acetyl-p-aminophenol;p-Acetamidophenol;p-Hydroxyacetanilide;Panadol;Paracetamol;Tylenol

Chemical Property of Acetaminophen Edit
Chemical Property:
  • Appearance/Colour:White crystalline powder 
  • Vapor Pressure:0.008Pa at 25℃ 
  • Melting Point:168-172 °C(lit.) 
  • Refractive Index:1.619 
  • Boiling Point:387.8 °C at 760 mmHg 
  • PKA:9.86±0.13(Predicted) 
  • Flash Point:188.4 °C 
  • PSA:49.33000 
  • Density:1.249 g/cm3 
  • LogP:1.42360 
  • Storage Temp.:Store at RT 
  • Solubility.:ethanol: soluble0.5M, clear, colorless 
  • Water Solubility.:14 g/L (20 ºC) 
  • XLogP3:0.5
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:1
  • Exact Mass:151.063328530
  • Heavy Atom Count:11
  • Complexity:139
Purity/Quality:

98% *data from raw suppliers

Acetaminophen *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • Hazard Codes:Xn,T,F 
  • Statements: 22-36/37/38-52/53-36/38-40-39/23/24/25-23/24/25-11 
  • Safety Statements: 26-36-61-37/39-22-45-36/37-16-7 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Other Uses -> Pharmaceuticals
  • Drug Classes:Nonsteroidal Antiinflammatory Drugs
  • Canonical SMILES:CC(=O)NC1=CC=C(C=C1)O
  • Recent ClinicalTrials:Assess the Safety, Tolerability, and Pharmacokinetics of AZD6234 Following Single Ascending Dose Administration to Healthy Subjects Who Are Overweight or Obese
  • Recent EU Clinical Trials:A Phase III Prospective, Randomized, Multicenter, Double-Blind, Placebo-controlled clinical study to evaluate the efficacy and safety of fixed dose combination (FDC) product Ibuprofen/Paracetamol/Phenylephrine Hydrochloride 200 mg/500 mg/10 mg film-coated tablets (containing Ibuprofen 200 mg, Paracetamol 500 mg and Phenylephrine Hydrochloride 10 mg) compared to Doregrippin? 500 mg/10 mg film-coated tablets (containing Paracetamol 500 mg and Phenylephrine Hydrochloride 10 mg) and Nurofen? 200 mg Tablets (containing Ibuprofen 200 mg) for the temporary relief of cold and flu symptoms, i.e. mild to moderate pain, sore throat, fever and nasal congestion.
  • Recent NIPH Clinical Trials:The comparison of post operative pain control between intravenous patient-control-analgesia and acetaminophen -a randomized controlled study-
  • Inhalation Risk:A nuisance-causing concentration of airborne particles can be reached quickly.
  • Effects of Long Term Exposure:Ingestion may cause effects on the kidneys and liver. This may result in impaired functions.
  • Drug interactions For patients with chronic alcohol ingestion or other liver enzyme inducers, especially barbiturates or anticonvulsants, when taking long-term or a large-scale use of this product, they may have a higher risk of liver toxicity.When combined with chloramphenicol, this product can prolong the latter t1/2 and enhance its toxicity.When combined with anticoagulant drugs, this product can increase the anti-blood-clotting effect. So it is necessary to adjust the dosage of anticoagulant drugs.When combining long-term large quantities of Acetaminophen with aspirin or other non-steroidal anti-inflammatory drugs, it will increase the risk of renal toxicity.When combined with the antiviral drug, zidovudine, it can increase the toxicity. We ought to avoid using at the same time. Potentially hazardous interactions with other drugs None known
  • Description Acetaminophen differs from the nonsteroidal anti-inflammatory agents described in that it is devoid of anti-inflammatory and antirheumatic properties. It was recently shown that acetaminophen, like aspirin, inhibits cyclooxygenase action in the brain and is even stronger than aspirin. On the other hand, the mechanism of analgesic action of acetaminophen is not fully clear, since it acts poorly on peripheral cyclooxygenase. Acetaminophen is an analgesic and antipyretic compound. Unlike many NSAIDs, which inhibit both COX-1 and COX-2, early studies suggested that acetaminophen is a poor inhibitor of both isoforms. However, it does inhibit COX-2 by 83% and COX-1 by 56% in human blood ex vivo, albeit at a high 1,000 mg dose, with IC50 values of 25.8 and 113.7 μM, respectively. Acetaminophen is enzymatically and non-enzymatically converted to several reactive metabolites that contribute to adverse or indirect effects, including liver injury. At toxic doses, the acetaminophen metabolite N-acetyl-4-benzoquinone imine (NAPQI; ) depletes glutathione reserves in the liver, leading to an accumulation of NAPQI and subsequent hepatocyte necrosis. Acetaminophen decreases glutathione levels and reduces glutathione peroxidase activity in mice when administered at a dose of 250 mg/kg and induces ferroptotic cell death in primary mouse hepatocytes, an effect that can be blocked by the ferroptosis inhibitor ferrostatin-1 . Acetaminophen has analgesic and antipyretic properties in animal models.
  • Uses Analgesic; antipyretic antiinfectant dispersing agent in liquid scintillation counting manufacture of azo dyes, photographic chemicals. Acetaminophen is widely used as an analgesic and fever-reducing agent. Acetaminophen is designed for moderate analgesia. It is also effective like aspirin and is used in analgesia for headaches (from weak to moderate pain), myalgia, arthralgia, chronic pain, for oncological and post-operational pain, etc.
  • Indications Acetaminophen (Tylenol) is an effective antipyretic and analgesic that is well tolerated at therapeutic doses. It has only weak antiinflammatory activity; thus, it is not useful in the treatment of rheumatoid arthritis and other inflammatory conditions.
  • Therapeutic Function Analgesic, Antipyretic
  • Clinical Use Acetaminophen is weakly acidic (pKa = 9.51) and synthesized by the acetylation of p-aminophenol. It is weakly bound to plasma proteins (18–25%). Acetaminophen is indicated for use as an antipyretic/analgetic, particularly in those individuals displaying an allergy or sensitivity to aspirin. It does not possess anti-inflammatory activity, but it will produce analgesia in a wide variety of arthritic and musculoskeletal disorders. It is available in various formulations, including suppositories, tablets, capsules, granules, and solutions. The usual adult dose is 325 to 650 mg every 4 to 6 hours. Doses of greater than 2.6 g/day are not recommended for long-term therapy because of potential hepatotoxicity issues. Acetaminophen, unlike aspirin, is stable in aqueous solution, making liquid formulations readily available, a particular advantage in pediatric cases.
Marketing and Price of Acetaminophen
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • AK Scientific
  • Acetaminophen
  • 500g
  • $ 147
  • Alfa Aesar
  • 4-Acetamidophenol, 98%
  • 1000g
  • $ 102
  • Alfa Aesar
  • 4-Acetamidophenol, 98%
  • 5000g
  • $ 374
  • Alfa Aesar
  • 4-Acetamidophenol, 98%
  • 250g
  • $ 38.1
  • Alfa Aesar
  • 4-Acetamidophenol, 98%
  • 500g
  • $ 63.5
  • ApexBio Technology
  • Acetaminophen
  • 5g
  • $ 42
  • ApexBio Technology
  • Acetaminophen
  • 10mM (in 1mL DMSO)
  • $ 55
  • ApexBio Technology
  • Acetaminophen
  • 10g
  • $ 57
  • Apolloscientific
  • Acetaminophen 98%
  • 250g
  • $ 53
  • Apolloscientific
  • Acetaminophen 98%
  • 500g
  • $ 69
Total 455 raw suppliers
Technology Process of Acetaminophen

There total 193 articles about Acetaminophen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With tetrachloromethane; tributylphosphine; In acetonitrile; for 41h; Ambient temperature;
DOI:10.1246/cl.1993.1369
Guidance literature:
With dihydrogen peroxide; at -40 ℃; for 0.5h; Product distribution; HF - SbF5;
Refernces Edit
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